Bad, but not hopeless for the demons. Humility is a difficult virtue to practice and Wormwood has a chance to ensnare him in it. Screwtape first proposes trying to get him to be prideful.
“Catch him at the moment when he is really poor in spirit and smuggle into his mind the gratifying reflection, ‘By jove! I’m being humble,’ and almost immediately pride - pride at his own humility - will appear. If he awakes to the danger and tries to smother this new form of pride, make him proud of his attempt - and so on.”
This is something discussed by Christ in the parable of the Pharisee and the tax collector. The Pharisee prays to God thanking Him for making him better than everyone else and more virtuous. Perhaps the best way to avoid this is not to declare that we’re not humble but simply to remind ourselves that we can be more humble and have failed to be humble in the past.
So then what is this humility that we are striving for? Screwtape says of the virtue that “By this virtue, as by all the others, our Enemy wants to turn the man’s attention away from self to Him, and to the man’s neighbours.” The easy way for Screwtape to counteract humility then is to pervert it so that the attention is refocused on the self.
“Let him think of it not as self-forgetfulness but as a certain kind of opinion…of his own talents and character. Some talents, I gather, he really has. Fix in his mind the idea that humility consists in trying to believe those talents to be less valuable than he believes them to be. No doubt they are in fact less valuable than he believes, but that is not the point. The great thing is to make him value an opinion for some quality other than truth, thus introducing an element of dishonesty and make-believe into the heart of what otherwise threatens to become a virtue. By this method thousands of humans have been brought to think that humility means pretty women trying to believe they are ugly and clever men trying to believe they are fools…. their minds (are) endlessly revolving on themselves in an effort to achieve the impossible.”
What Screwtape is saying is that if humility is about not taking joy in our gifts, then the focus is still on ourselves and not on God. It is also focusing on falsehood which is contrary to the truth that is Christ. Instead a realistic and accurate portrayal of our abilities is necessary.
Screwtape goes on to discuss how true humility is practiced. What it means is to be indifferent to the fact that we have the gifts. That is, if we’re arguing with the people in free speech alley, it doesn’t matter who delivers the logical blow that topples their house of cards. It matters that the blow is delivered and we should rejoice in the accomplishment in argumentation. Humility then is an indifference to the self which allows us to more fully love others and most importantly love God. The paradox is, as Screwtape points out, that “when they have really learned to love their neighbors as themselves, they will be allowed to love themselves as their neighbors.”